


One Night but Two Times that Night

by HeartBash



Category: Crazy Ex-Girlfriend (TV)
Genre: 3x02, Canon Compliant, F/M, Fluff and Angst, Fluff and Smut, Nathaniel's POV, Resolved Sexual Tension, Season/Series 03, Sex
Language: English
Status: Completed
Published: 2017-12-31
Updated: 2018-02-21
Packaged: 2019-02-25 22:54:34
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 4,903
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13222944
Author URL: https://archiveofourown.org/users/HeartBash/pseuds/HeartBash
Summary: What happened between Nathaniel & Rebecca the night of the masquerade party? What is the one thing Nathaniel wanted to do with Rebecca? Why did he think they were “love making” that night? And why did he think he knew Rebecca so well after spending only one night together?





	1. The Deal

**Author's Note:**

> This is a story that attempts to explain what happened the night that Rebecca and Nathaniel had sex "one night, but two times that night." 
> 
> Bonus points for anyone who can find the subtle reference(s) to my other favorite show.

Nathaniel was in the middle of a proverbial legal minefield. He let one of his subordinates come into his home and literally proposition him for sex in exchange for favors. Could it be any more textbook wrong? And he knew in the eyes of the state of California it doesn’t matter whether the acts take place off work premises or not. Despite all the mental alarm bells, when she was in his lap, running her hands over his shoulders, he was putty in her hands. 

Since he met her, he had been intrigued by Rebecca. At first, it was just a fascination with why a woman as smart, educated, and accomplished as her would be working in West Covina. Then, his curiosity grew when he discovered that the supposed “man of her dreams” appeared to be a slow-witted bro. Frankly, he thought she deserved better in both areas of her life. It became obvious that she was a complex person. And the more he found out about her, the more he wanted to know.

The dream about her took him by surprise. It forced him to admit that he was subconsciously also harboring a physical attraction to her. The very next day, when the elevator malfunctioned, it almost felt like a sign from the universe. This was an opportunity to get closer to her. After she spurned his straightforward proposal to simply have sex (yet another huge legal misstep, he acknowledged), they ended up talking for hours. It was truly mystifying to him how they could be so similar in some ways and such polar opposites in others. He felt her defenses slowly fall away as they talked and in some moments he felt that they were really connecting. The chemistry between them was palpable.

When they came close to kissing, he waited for her to make the final move. Since she had rejected his advance earlier, he wanted no ambiguity about her decision to kiss him. But then the elevator started working again and the moment was lost. He went through a range of emotions from disappointment to hope that maybe he could salvage the situation to acceptance that it just wasn’t going to happen. It was probably for the best anyway. He wouldn’t want to be the scapegoat any discord between she and Josh. But suddenly she grabbed his neck and kissed him soundly. It lasted mere seconds, leaving no time for him to react. She looked panicked and ran out of the elevator as soon as the doors opened. He was left speechless, again totally bewildered by her.

After that night, he couldn’t get her out of his head. He wanted to learn more about her, be closer to her, kiss her again. He couldn’t seem to stop replaying images of the dream and the kiss in his mind over and over. When she put up a firm boundary about a kiss never happening again, he respected it. She was busy planning her wedding anyway so he tried to rid her from his mind and not interfere in her life. But when she looked so sad and vulnerable about her dad not attending her wedding, his heart went out to her. He felt the uncharacteristic urge to gather her in his arms and protect her from the outside world of hurt. And this kind of hurt he knew all too well. He decided to fly in her father despite the deal he made with himself. The moratorium on Rebecca would start after the wedding.

Watching Rebecca be abandoned at her wedding made him feel protective of her all over again. He tried every form of communication to get in touch with her after the wedding, masking his concern behind professional appearances. When he finally broke down and went to her home, using a gift basket as a pretense to visit, he had no plan for what he would say. He just wanted some kind of confirmation that she was ok.

He was completely shocked when she returned to work transformed into an aloof, confident, sexy woman-scorned living trope. He knew there was no way she bounced back from being abandoned that fast. If there was one thing he knew about her, it was that she felt things deeply. At the same time, her new persona was intoxicating and he felt a rush of adrenaline whenever he was around her. He was a moth drawn to the flame burning around her. Which, of course, lead him to his most current predicament. His willpower quickly crumbled at the promise of a full night with her. And he used every high-powered contact and stored-up favor he had to give Rebecca what she wanted. 

The night of the masquerade party, he couldn’t take his eyes off her. Besides the fact that she looked stunning, he couldn’t help but overhear her conversations with the women at the party. She was her old bubbly, quirky self again, just barely skirting the topics he told her to avoid. He was enchanted by her. 

Dancing with her felt like the right thing to do in the moment and it was an excuse to hold her close to him. When they kissed, it happened so organically he didn’t know which one of them initiated the contact. She pressed herself against him as they kissed and he was getting the feeling that she wanted this as much as he did. He felt a warmth in his chest and butterflies in his stomach.

“Let’s get out of here,” she breathed with a mischievous smile.

“Uh huh,” was all he could muster.

Nathaniel lead her toward the exit with a hand on the small of her back. He quickly texted his driver to pull around. A black limousine pulled up to the curb moments after they exited the building. Rebecca waggled her eyebrows at him, impressed. He opened the door for her and then followed her inside. “Could you take us to my apartment, Chuck?” The driver nodded and then rolled up the window separating the driver’s seat from the back.

Rebecca gazed starry-eyed out the window with her lips parted. He felt like his body was buzzing. He tentatively put his hand on the inside of her thigh and he heard her breath hitch in her throat. He stroked the skin there softly with his thumb and noticed her chest rapidly rising and falling. He desperately hoped that she wanted this as much as he did. He felt her subtly shift her weight to lean into him and saw goosebumps raised on her arm.

By the time they reached his apartment building, he felt like he may pass out from the sheer anticipation. He was barely touching her but he felt an electricity between them. When the limo stopped at his apartment building, he became laser-focused on getting inside as quickly as possible. They stepped inside the elevator and he rapidly hit “3” more times than necessary. He saw a hint of a smile on Rebecca’s face from his obvious impatience. The door closed and then the elevator hitched. Both Rebecca and Nathaniel’s eyes widened in horror.

“Oh god no,” she exclaimed, pushing Nathaniel out of the way and jamming the button several times, betraying her cool exterior. The elevator then suddenly sprung to life and they both breathed a sigh of relief. He chuckled, “Can you imagine?” She shook her head, visibly shaken. Finally at the apartment door, he fumbled with his keys for what felt like an eternity. 

“You are going to freaking kill me,” Rebecca said with frustration. But then the lock gave way and they spilled into the apartment.

Once they crossed the threshold, he cupped her face with both hands and kissed her deeply. He backed her up against the door, which closed with a thud. She whimpered from the pain but grabbed his shirt and pulled him against her, urging him to keep kissing her. She frantically tried to undo the buttons of his shirt. After failing to make any progress, she pulled away and said, “Hey, could you help me out here.” He made short work of it, discarding his shirt on the ground. She ran her hands over his bare shoulders and arms appreciatively. He captured her lips again and ran his hands all over her body. After several moments he stopped and rested his forehead against hers.

“Hey, let’s move this to-” she panted, tilting her head toward the bed. She grabbed his hand and led him there, lying down on her back and pulling him to follow. He covered her body with his and she immediately enveloped him with her legs. She wrapped her arms around his neck, tugging him down to resume kissing her.

His head was swimming with desire, but the deal still weighed heavily on his mind. He knew that Rebecca’s over-the-top sexy persona was a facade and she had to still be hurting from the wedding. He didn’t want to take advantage of that vulnerability under the guise of this ill-conceived deal. Yet, at the same, he had been paying rapt attention to her all night and felt that all signs pointed to the fact that she wanted him back. Even though it would be painful to stop, he needed to hear that confirmation from her. 

He pulled away and looked deeply into her eyes, “Hey, you don’t have to do this, you know...regardless our deal.” 

She paused a moment and he held his breath. Her eyes were dark with desire. “I want to. I’ve always wanted to.” She drew him back down to her.

The words reverberated in his mind. She’s always wanted to. Always.


	2. The First Time that Night

**Summary for the Chapter:**

> What happened between Nathaniel & Rebecca the night of the masquerade party? What is the one thing Nathaniel wanted to do with Rebecca? Why did he think they were “love making” that night? And why did he think he knew Rebecca so well after spending only one night together?

**Notes for the Chapter:**

> This is a story that attempts to explain what happened the night that Rebecca and Nathaniel had sex "one night, but two times that night."
> 
> Warning: There are descriptions of sex in this chapter. 
> 
> Bonus points for anyone who can find the subtle reference(s) to my other favorite show.

The words reverberated in his mind. She’s always wanted to. Always. 

Nathaniel felt emboldened by Rebecca’s declaration. She had wanted him from the beginning. These feelings weren’t one-sided. He hadn’t just imagined the chemistry between them. Maybe all those times he had intrusive thoughts about kissing her again, touching her...maybe she had those thoughts too. And now she was under him, arching her back to meet his touch. 

He dragged his hand slowly down her body, savoring the swell of her hip and then her upper thigh. He found the edge of her dress and slipped his hand underneath.

She gently pushed on his chest and he took his hand away. 

“Sorry,” he apologized, panting. 

“No, no... Listen, I have a complicated series of pulleys and levers keeping me in this dress,” she huffed with a smirk. “You’re not going to be able to get me out of this thing.” 

“Ok…” he smiled. She pushed on his chest again and he took her cue to untangle himself from her limbs.

She got off the bed and walked to the corner of the room, her heels clicking against the hardwood floor. He fidgeted, unsure what to do. “Listen, this process is going to be incredibly unsexy to watch. Can you just...” She twirled her finger in a circular motion.

“You want me to turn around?” he asked, incredulously.

“I don’t want to ruin the illusion of how effortlessly sexy I am. You think this,” she gestured up and down her body, “just happens?!”

He let out a small laugh and turned to face the other way. He busied himself by pulling a condom out of the drawer of the nightstand and setting it on the top. He heard a series of grunts from the corner where Rebecca was undressing.

“You ok over there?” he asked while unbuckling his pants. 

“Yep, doing great! Boobs in t-minute 10 seconds.”

He smiled to himself and then a thought dawned on him. “Hey, could you also...take your hair down?”

She was silent for a moment. “Uh, sure. Whatever you want, remember?” He heard the clink of bobby pins hitting the surface of his dresser. It bothered him a little that she was still alluding to their deal, but he decided to push the thought aside. She said that she wanted this. He took off his boxers and suddenly felt nervous. 

“Ok,” Rebecca purred in an affected, sexy voice. 

He turned around and she was just a few steps away from him, fully naked. Her dark hair fell around her face in messy curls and her lipstick was smudged. His mouth was suddenly dry. “Wow,” was all he could say. 

Her eyebrows climbed high on her forehead, “You really haven’t been with someone bigger than size 2, huh?” 

“No, no, it’s not that. You’re...” he exhaled sharply, completely lost for words.

Her eyes slowly trailed down his body and he felt hot under her gaze. She bit her lip and she smiled, apparently pleased with the appraisal. Then their eyes met. She closed the space between them and wrapped her arms around his neck. “So...what do you want?” she asked seductively, still playing the vixen. 

“You,” he replied earnestly and then kissed her. He gently edged her backward until her knees hit the bed’s edge. She laid back and he followed. As they shamelessly made out, she dragged her hands up and down his back, urging him to press against her. Each time he did, her hips rose to meet his. She started making soft, whimpering sounds and the sensory overload made him realize he had to slow down. He lifted his hips away from hers and started kissing along her collarbone. He then started kissing his way down her body, the intention of his journey clear.

“Hey wait,” she said and he stopped and looked up at her. “I really appreciate the sentiment and I would love for you to do that another time...but we’ve had months of foreplay and I just want…” and her eyes darted to the condom on the nightstand. He smiled, happy that she was expressing what she wanted from him.

“Are you sure? I’m happy to…”

“God, I’m sure. Please just…” she seemed to be having a hard time formulating any more complete sentences.

He got up and made quick work of putting the condom on himself. Then he resumed his position on top of her and angled himself at her entrance. She had her eyes closed and her mouth open, in an expression he was starting to recognize as her aroused face. She was breathing heavily in anticipation. He slid his arms under her back and threaded his left hand through her hair, cradling her head. 

He pushed into her slowly. He stopped moving when her face changed to a pained expression. “It’s the good kind,” she anticipated his question without even opening her eyes. A subtle smile played at her lips. She exhaled deeply, “Please god keep going.”

He obeyed and established a slow rhythm. 

“Hey,” he said gently. She opened her eyes and the intensity in her face took his breath away. She looked aroused and vulnerable. “Nathaniel,” she said softly, almost like she was seeing him for the first time. He couldn’t remember the last time he had a moment with a woman that felt this intimate. He hoped she saw in his face how much he wanted her, all of her. Her eyes darted down to his lips and he kissed her.

He reveled in the feeling of holding her head in his palm. It felt like he was completely possessing her. She started making a humming sound low in her throat, and the sound shot straight through him. 

While she seemed to be enjoying herself, he started to worry that she wouldn’t climax in their position. And there was no way he was going to walk away from this night without seeing her face when she orgasmed. He wanted to see her completely lose control.

He broke the kiss and shifted off of her. He sat up with his back against the headboard. She followed wordlessly and straddled him, easily sliding back down on him. They were face-to-face now and she wrapped her arms around his shoulders while he held her against his chest. “I want you to take control,” he whispered. She simply nodded and and started moving up and down on him slowly. He watched her face in rapt attention as she tested different angles to find what was pleasurable for her. He loved how unabashedly self-possessed she was in her sexuality. Finally she scrunched her face and he knew she had found the spot. With each thrust now her clit was grinding against his pelvic bone. He tried to replicate the movement with each push into her.

He buried his face in her neck, kissing her there and tasting her sweat. She started to speed up and her little moans and gasps were proving to be his undoing. He could tell she was almost there and wanted to give her the push over the edge. 

He had a pet theory, developed over his many sexual conquests, that smart women like dirty talk during sex. He whispered into her neck, “Rebecca, you’re so sexy.” She threw her head back, eyes shut and mouth agape. “Oh god, keep going,” she said. He wasn’t sure if she meant his movements or the talking, so he met her thrusts harder and said, “I want to see you come, Rebecca.” And that was it. Her face went slack and she let out a guttural moan, “Oh my god, yes, yes, yes.” He couldn’t hold on any longer and exploded inside of her. 

She collapsed on him, her arms around his neck and her head lolling on his shoulder. He wrapped his arms tightly around her back and held her while they both caught their breath. His heart felt like it was about to pound out of his chest. He rubbed his hands over her back soothingly. 

After several minutes of holding each other, Rebecca got off of him carefully and then silently walked to the bathroom and shut the door. He got up and disposed of the condom and then laid back down in the bed to wait for her return. He heard the toilet flush and she came back into the bedroom. Her chest was completely flushed red and she had a demure smile on her face. He was relieved that she seemed pleased. 

For a moment they just looked at each other, both smiling shyly. “You’re going to stay, right?” he asked hesitantly. 

“Yea, is that ok?” she asked in a small voice. He nodded. He suddenly felt very vulnerable.

“Hey, I obviously can’t sleep in that dress. Could I borrow something?” she asked.

“Of course. Take anything you want. Go in the - “ Before he could finish, she disappeared into the entryway of his apartment and came back wearing the white shirt he wore earlier. 

“Does this do anything for you?” she asked in a mock-seductive voice. Her relaxed demeanor put him at ease.

He grinned. “Yea, come here,” he said, pulling back the blankets for her to join him. She gladly slid under the blankets and laid beside him so they were facing each other. He leaned over and turned off the light. The room flooded with darkness except for sparse streaks of moonlight escaping through the window. He put an arm around her waist and settled himself so their faces were mere inches away from each other.

“Hey,” she whispered in the darkness, “I’m curious...what is the thing you wanted to do tonight?”

“What do you mean?”

“Remember I said you could do anything you want tonight? Are you sure we did it? I mean, don’t get me wrong, it was great...”

“Don’t worry about it,” he cut her off, hoping she would just drop it.

“Oh no, come on, tell me.” She wiggled closer to him.

He cleared his throat. “We did what I wanted so we’re good.”

“Interesting…” She sounded even more intrigued.

“Ok, if I tell you, you have to promise you won’t mock me,” he said.

“Ok, now you have to tell me! Please please,” she pouted.

He paused for a moment, debating whether to tell her. “So, I had this...dream about you when we first started working together,” he started. He expected some quip or other reaction from her, but she was silent. “We were having sex...I was on top of you…” He trailed off, beginning to feel self-conscious about this admission. “Never mind. Just don’t worry, we did what I wanted.”

She was still silent and he wished he could see her face in the darkness. “I’m seeing a whole new side to you, Nathaniel,” she finally said.

“Is that a good thing?”

“I like it,” she said softly. “So why the big-bad-scary-boss song and dance at work? Seems like maybe you’re kind of a softie.”

“I could ask you the same question,” he replied. “Why the ‘espresso-haired vixen’ routine all of a sudden?” 

She was quiet for a long time and he again wished he knew what she was thinking. He moved closer to her and cupped her face in his hand. He rubbed his thumb over her cheek and found dampness there. “Hey, what’s going on?” he whispered. 

He felt her shake her head. She was crying but made no sound. “Um, sorry. Listen, I know I’ve been acting all detached and above-it-all lately,” she paused. “The truth is I’m broken. I’m fucked up,” her voice caught in her throat. 

“Rebecca, no one could possibly blame you for being hurt by what happened at the wedding. Not to mention the shit your dad pulled,” he reassured her. “Listen, you don’t have to pretend in front of me. I don’t buy that uncaring, hot and tough act for a second.”

“Yea, but you kinda liked it,” she said with a smirk in her voice.

“Ok, yea, I did think it was kinda sexy,” he conceded. “Rebecca listen, everyone is fucked up. You think I haven’t done some messed up stuff in my life?” He wiped away her tears with his thumb and then wrapped his arm tighter around her. She nuzzled into his chest and let out a deep exhale. He felt her body relax. Soon, her breathing evened and he joined her in sleep shortly after.


	3. The Second Time That Night

When Nathaniel stirred the next morning, the first thing he became aware of was her scent. He breathed in and realized his nose was buried in her hair. It smelled faintly floral and feminine and just completely...her. He wanted to live in it. 

He didn’t remember changing positions during the night, but he was now spooning her, one of his arms heavily draped over her midsection and the other supporting her head under the pillow. He sighed and pulled her closer, savoring the feeling of her warmth and softness against him. 

He felt Rebecca shift in his arms and his eyes snapped open. He wasn’t sure if post-coital, next-day cuddling was part of the deal. But her eyes were still closed and she was clearly still in a half-sleep state. She wore a soft smile and ran her hand lazily up and down his arm. She finally settled her hand over his, threaded their fingers together, and then guided his hand under her chin and snuggled against it. He couldn’t help feeling an overwhelming tenderness toward her and hoped that maybe this had been more than just a one-night stand.

He took a chance and nuzzled her neck, planting a few kisses there. 

“Hmmm...hi,” she mumbled, her eyes still closed. 

“Hi,” he responded, his voice low and scratchy. 

“You feeeel gooood,” she said sleepily, stretching the words out luxuriously and squeezing the hand that was still enmeshed with hers. “Just a couple more hours, ok?” she muttered. He felt her body relax against him like she might fall back asleep. 

He let her have a few moments of contentment but he had other plans for her. He untangled his limbs from hers and she let out an annoyed grunt in response. “Nooooo…” she sighed.

“Shhh...you just lie back and relax,” he soothed. He pushed the blankets back and traveled down her body until his face was settled between her legs. She finally opened her eyes and looked down at him with an arched eyebrow. 

He smiled in response and pushed the dress shirt up until he had full access to her. 

“Is this ok?” he asked.

She rolled her eyes in response and then bent her knees to open herself further to him.

He began trailing feather-light kisses along the inside of her thighs. She rested her head back on the pillow and exhaled. He kissed up and down along each thigh, but every time he got close to the place she wanted him the most, he backed off. She pushed her hips forward and he assumed it was an attempt to wordlessly communicate that she needed more.

He stopped kissing her. “What do you want?” he asked devilishly. She bit her lip and let out a frustrated sound that was between a moan and a whimper. 

But she was stubborn and he knew she didn’t want to give him the satisfaction. “You dick…” she said, her voice dripping with venom and lust. He resumed kissing her inner thigh with more pressure this time, getting so so close. Then he switched to licking with the flat of his tongue. He could smell how aroused she was.

“I can stop if you want.” With that, she had had enough of the teasing. She reached down and grabbed the back of his head, pressing him against her. He relented and finally pressed an open-mouthed kiss against her clit. He heard her mutter a curse and her legs twitched. Not sparing a moment, he put all his effort into alternating between licking her and sucking her clit. She writhed against him and moaned openly. One of her hands bunched up the blankets in a fist at her side and the other she rested on the back of his head, stroking the short hairs there.

After several minutes of his efforts, he started to tease at her entrance with his finger. She grabbed at his head and shoulders to get his attention. She wanted something but apparently had lost all ability to speak. “Is this what you want?” he asked breathlessly and looked up at her. She shook her head and pulled at his shoulders, signalling him to join her. He wasn’t ready to stop. He was just getting the rhythm and feel for how she liked to be pleasured.

But then she finally said in a labored voice, “No, I want to feel you,” and he couldn’t refuse. He got up and quickly got a condom from his nightstand and rolled it on while she watched him through hooded eyes. Once he was ready, she turned her back to him and he surmised she wanted to resume their previous spooning position. He slid one arm under her head and threw the other around her waist, pulling her back into his body. It felt heady and masculine to completely engulf her body with his. He thought about taking off her shirt but there was something extremely arousing about fooling around with her in his shirt. 

He positioned himself to enter her and she pushed her ass back against him eagerly. He gently swept her hair back, exposing her neck and ear to him. He kissed behind her ear and then slowly thrust into her. She sighed with relief. 

After finding a rhythm, he took her hand in his and guided it down to her clit. He was struck by how small her fingers were next to his. “Show me how to touch you,” he whispered in her ear. She shivered and then started rubbing herself using his fingers. She was slick from his earlier ministrations.

“Hey, you remember that night in the elevator?” he whispered in her ear.

Her eyes cracked open and she looked at him sideways. “Yea,” she exhaled with a whimper. She arched her back against him, craving more. He obliged and thrust into her harder. She bit her lip and groaned.

“I wanted to take you up against the wall right there.” 

Her mouth fell open. “Yea?” she breathed.

“Mmm hmm,” his voice rumbled deep in his chest. “Did you want me?”

She huffed with exasperation. He suddenly stopped all his movements. She looked over her shoulder at him and he grinned.

“Oh my god, you are such an asshole.” She tried to angle her hips back against him but he pulled away further.

“An asshole you want to fuck in an elevator...” he said and punctuated his point by roughly shoving into her again.

She cried out. “...or bend you over a desk,” he finished. With that, she was coming hard, clenching around him. And watching her fall apart, he felt his own orgasm taking hold and couldn’t stop it. “Rebecca,” he growled into her ear and he held her hips still against him as his jerked erratically. 

He panted against her neck as he came down from the high of his orgasm. Once he regained his faculties, he released her and collapsed onto his back. She did the same, looking up at the ceiling and putting her hand over her heart under the dress shirt. 

“Whew!” she blurted out. He smirked. 

After a few minutes he felt his heartbeat finally slow and Rebecca cuddled up to his chest. “That was actually very satisfying.”

“Isn’t it always?”

**Author's Note:**

> Email: heartbashfic@gmail.com


End file.
